Phenylethanolamine → N-[2-(4-Methylphenyl)-1-methylethyl]-2-hydroxy-2-phenyl ethanamine
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH3:10])=[CH:4][CH:3]=1.[OH:12][CH:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:14][NH2:15]>C1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:15][CH2:14][CH:13]([OH:12])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:10])=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 4-methylphenylacetone (2.7 g) and 2-hydroxy-2-phenylethanamine (2.5 g) was refluxed in benzene (70 ml) under Dean & Stark conditions for 4h. The solvent was removed under reduced pressure, replaced with methanol (100 ml) and cooled in ice during the portionwise addition of sodium borohydride (3.0 g). The solution was stirred for 2 h, the solvent was evaporated under reduced pressure and the residue was partitioned between water (100 ml) and chloroform (100 ml). The organic extract was dried (MgSO4), the solvent was evaporated and the residual oil was crystallised from hexane to give the title compound (2.1 g) as a 44:56 mixture of diastereoisomers, mp 74°-94°.
Workup
- customThe solvent was removed under reduced pressure
- temperaturecooled in ice during the portionwise addition of sodium borohydride (3.0 g)
- customthe solvent was evaporated under reduced pressure
- customthe residue was partitioned between water (100 ml) and chloroform (100 ml)
- extractionThe organic extract
- dry with materialwas dried (MgSO4)
- customthe solvent was evaporated
- customthe residual oil was crystallised from hexane
Sources & evidence
- ORD record
- ord-8b37eed88d3046659cfdd7178b96aaf3
- Source dataset
- uspto-grants-1986_05
- Patent number
- US04588749
Reaction notes
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